How To Smoke A Cigar With Your Boss Without Looking Like An Amateur

Eli Epstein / Business Insider
So you just closed your first big deal and it's time to celebrate. Your boss invites you upstairs to the boardroom where the executives are lined up at the long oak conference table, premium cigars by their sides to mark the occasion.

One by one they light up, oaky musks wafting, and finally it's your turn to spark your earthy blend. There's just one problem—you're totally clueless.

"The smoking is supposed to be the fun part," said Michael Herklots, world-class tobacconist and Executive Director of Retail and Brand Development at Nat Sherman, a cigar emporium in midtown Manhattan. "The last thing you want to do is fumble -- to light or cut the wrong end."

How does one avoid these fatal flubs? We sat down with Herklots to find out the best ways to prove your worth when it comes time to lighting up the celebratory Maduro. Puff away, novices.

First of all, don't overthink your smoke

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Beginning smokers can have three separate reactions to being handed a cigar. They can freeze and not know what to do with it, they can overreact and try to reinvent the wheel in cutting and lighting it, or they can calmly approach cigar smoking as a leisure activity capable of mastery.

The greatest risk, Herklots warns, is becoming over-involved with cigar nuances at the beginning. "Don't get caught up in the fanfare and be intimidated by it so you start feeling like you're doing something wrong," he says.

Instead, Herklots advises novel smokers to stay away from a "right versus wrong" motto. He agrees that there are ideal ways to cut a cigar, but he also says there are plenty of other ways to do it correctly.

Under pressure, just get the job done. Don't overdo it.

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Choose the right cigar: smaller isn't necessarily better for a beginner

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While the head honchos in the boardroom will be smoking heavier blends, it's important for you not to overdo it and cough up a storm. There's nothing wrong with choosing a premium mild cigar. Your bosses will respect you more for knowing what you want and not guessing blindly. This is where things can get dicey, says Herklots.

"The biggest mistake new cigar smoker make is in the format they pick," he says. "New smokers tend to smoke something shorter, thinner, and overall, smaller. The problem with this is that the shorter a cigar is, the closer the hot part is to your mouth. It gets hotter faster, which is not a pleasant experience if you're starting out."

Herklots makes an analogy here to using a regular straw versus a cocktail straw. With a regular straw, you have a wide cylinder with a long body that allows you to draw substance out over a longer period of time. If you use a cocktail straw, on the other hand, the experience is more aggressive and concentrated. The same goes for cigars. A long, fat cigar is a milder, cooler, and longer-lasting cigar. A shorter one is an intense experience better enjoyed by veteran smokers.

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A simple tip for cutting your cigar

A well-cut cigar
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All hand-rolled cigars are closed off with a cap to ensure that they don't unravel and dry out. Removing this cap is essential to a good smoke, and there are a few ways to do so, none of which are wrong. Herklots, though, recommends the straight cut made by a guillotine cutter.

A tip he shared with us involves laying the cutter flat down on a surface and then bringing the two blades in and clipping the head. By placing the guillotine on its belly, smokers can ensure they don't over-cut the cigar.

Trying to smoke an uncut cigar is a sure-fire way to make a fool of yourself. You want to make sure you get your cigar cut, whatever the method may be.

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There is one kind of lighter you should NEVER use

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You've mastered the cut and now it's time for the easy part: the light. While tobacconist Michael Herklots stresses the importance of just getting the cigar lit and ignoring expert nuances, he stresses the importance of avoiding one glaring mistake: using the incorrect type of lighter.

Wooden matches are desirable. butane lighters work, but Zippos do not. Herklots warns that you DO NOT, under any circumstances, want to introduce foreign substances into your cigar. This will greatly affect the taste and your bosses will look at you askew if they see you flipping open your Zippo, about to ruin the $40 cigar they just handed you.

The best strategy is to ask for a match box, take two matches, and then light them against the striker. Once this is done, place the cigar in your mouth and delicately puff on it while lighting the uncut end. With your free hand, rotate the cigar so it doesn't light unevenly. When the outer rim of tobacco begins to glow, you're good. Blow out the match and start shaking a few hands.

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Finally, it's time to smoke: remember, it's not a cigarette

How we smoke at Business Insider
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You will learn quickly that cigars are not meant to be inhaled. If you make the mistake of doing so, you will surely be met by a maelstrom of coughing and wheezing. This, let us warn you, is quite embarrassing. Those around you will know you don't share their sacred hobby.

"You need to get used to the act of drawing and expelling without inhaling and exhaling," says Herklots. "Once you get it, it's about practice, but this is a hell of a lot more fun to practice than other things."

Experts have mastered the breathing and exhalation patterns, but you don't need to be a connoisseur to learn how to do it the right way. Cigars are about taste, and to best appreciate their flavors, you need to draw slowly and infrequently, a few times per minute. Then, swirl around what you've taken in and let it reach the back of your mouth before gently expelling it. This way your whole mouth experiences the act.

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Know how to talk about the taste

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Even if you're not the most experienced smoker, your superiors will still appreciate your attention to detail and perspicacity when smoking. How does the cigar taste for you? Does it change taste as it's smoked? How is the smoke acting on your palate?

Try to ask these questions when you're with more advanced smokers. If their cigar guys, they'll be excited to discuss what they're experiencing. Plus, they'll be impressed that you're paying attention to the finer points of their hobby.

"Taste is the most popular way to talk about cigars, and there's no wrong answer," says Herklots as we enjoy two different Dominican cigars from Nat Sherman's Metropolitan Collection, one fermented to be Maduro.

We talk about the cigars' strength -- relatively mellow -- and then their bodies -- which Herklots describes as the taste when the smoke hits your palate. He says "woodsy." I say "oaky." Again, he stresses, there is no wrong answer.

Herklots also notes the placement and behavior of his cigar. He says his focuses on the tip of his tongue and has a drying effect.

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Be inquisitive--or at the very least, appreciate the hobby

Cigars from the Nat Sherman Townhouse in New York City
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Your bosses will appreciate your curiosity. It helps when you show interest in their hobby and their smoking experience, and it's even better when you show them you want to learn a bit more. This way, you show them you know the basics, but also that you want to gain some of their knowledge.

Ask them the origins of their blend -- where are the filler and binder from? What about the wrapper? Ask if they prefer Maduros to Claros (brownie points if you know these are wrapper types), or a Torpedo to a Robusto (cigar shapes).

Just don't be pedantic. This is a hobby for these guys. Unless you're in their circle, let them do the heavy lifting.

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Put out your cigar and call it a night

With the deal closed and the cigar almost half-way smoked, you may want to put it out and call it a night. There's no shame in this, just don't treat the cigar like a half-eaten hamburger. You can't just doggy bag it. Once it's done, it's done. So if you find yourself finished, politely let the cigar burn out in the ashtray (don't demolish the wrapper and reveal its insides -- this looks sloppy and novice).

Then, try to schedule another smoking session with the higher ups. Chances are if you didn't embarrass yourself by lighting the wrong end or wheezing till no end, they'll want to invite you into their cigar cadre.

Remember your experience though. Cigar smokers can be geeky and obsessive about their hobby, and you'll want to return the next week to compare and contrast what you've smoked.